DES is now considered to be insecure for many applications. This is chiefly due to the 56-bit key size being too small; in January, 1999,
distributed.net
and the Electronic Frontier Foundation
collaborated to publicly break a DES key in 22 hours and 15 minutes (see chronology). There are also some analytical results which demonstrate theoretical weaknesses in the cipher, although they are infeasible to mount in practice. The algorithm is believed to be practically secure in the form of
Triple DES, although there are theoretical attacks. In recent years, the cipher has been superseded by the
Advanced Encryption Standard
(AES). Furthermore, DES has been withdrawn as a standard by the National Institute of Standards and Technology
(formerly the National Bureau of Standards).

Some documentation makes a distinction between DES as a standard and DES as an algorithm, referring to the algorithm as the
DEA
(Data Encryption Algorithm).

The origins of DES go back to the early 1970s. In 1972, after concluding a study on the US government's
computer security
needs, the US standards body NBS (National Bureau of Standards) — now named NIST
(National Institute of Standards and Technology) — identified a need for a government-wide standard for encrypting unclassified, sensitive information.[1]
Accordingly, on 15 May 1973, after consulting with the NSA, NBS solicited proposals for a cipher that would meet rigorous design criteria. None of the submissions, however, turned out to be suitable. A second request was issued on 27 August 1974. This time, IBM
submitted a candidate which was deemed acceptable — a cipher developed during the period 1973–1974 based on an earlier algorithm, Horst Feistel's
Lucifer
cipher. The team at IBM involved in cipher design and analysis included Feistel, Walter Tuchman,
Don Coppersmith, Alan Konheim, Carl Meyer, Mike Matyas,
Roy Adler,
Edna Grossman, Bill Notz, Lynn Smith, and
Bryant Tuckerman.

On 17 March 1975, the proposed DES was published in the
Federal Register. Public comments were requested, and in the following year two open workshops were held to discuss the proposed standard. There was some criticism from various parties, including from
public-key cryptography
pioneers Martin Hellman
and Whitfield Diffie,[2]
citing a shortened key length
and the mysterious "S-boxes" as evidence of improper interference from the NSA. The suspicion was that the algorithm had been covertly weakened by the intelligence agency so that they — but no-one else — could easily read encrypted messages.[3]
Alan Konheim (one of the designers of DES) commented, "We sent the S-boxes off to Washington. They came back and were all different."[4]
The United States Senate Select Committee on Intelligence
reviewed the NSA's actions to determine whether there had been any improper involvement. In the unclassified summary of their findings, published in 1978, the Committee wrote:

In the development of DES, NSA convinced
IBM
that a reduced key size was sufficient; indirectly assisted in the development of the S-box structures; and certified that the final DES algorithm was, to the best of their knowledge, free from any statistical or mathematical weakness.[5]

However, it also found that

NSA did not tamper with the design of the algorithm in any way. IBM invented and designed the algorithm, made all pertinent decisions regarding it, and concurred that the agreed upon key size was more than adequate for all commercial applications for which the DES was intended.[6]

Another member of the DES team, Walter Tuchman, stated "We developed the DES algorithm entirely within IBM using IBMers. The NSA did not dictate a single wire!"[7]
In contrast, a declassified NSA book on cryptologic history states:

In 1973 NBS solicited private industry for a data encryption standard (DES). The first offerings were disappointing, so NSA began working on its own algorithm. Then Howard Rosenblum, deputy director for research and engineering, discovered that Walter Tuchman of IBM was working on a modification to Lucifer for general use. NSA gave Tuchman a clearance and brought him in to work jointly with the Agency on his Lucifer modification."[8]

and

NSA worked closely with IBM to strengthen the algorithm against all except brute force attacks and to strengthen substitution tables, called S-boxes. Conversely, NSA tried to convince IBM to reduce the length of the key from 64 to 48 bits. Ultimately they compromised on a 56-bit key.[8]

Some of the suspicions about hidden weaknesses in the S-boxes were allayed in 1990, with the independent discovery and open publication by
Eli Biham
and Adi Shamir
of differential cryptanalysis, a general method for breaking block ciphers. The S-boxes of DES were much more resistant to the attack than if they had been chosen at random, strongly suggesting that IBM knew about the technique in the 1970s. This was indeed the case; in 1994, Don Coppersmith published some of the original design criteria for the S-boxes.[9]
According to Steven Levy, IBM Watson researchers discovered differential cryptanalytic attacks in 1974 and were asked by the NSA to keep the technique secret.[10]
Coppersmith explains IBM's secrecy decision by saying, "that was because [differential cryptanalysis] can be a very powerful tool, used against many schemes, and there was concern that such information in the public domain could adversely affect national security." Levy quotes Walter Tuchman: "[t]hey asked us to stamp all our documents confidential... We actually put a number on each one and locked them up in safes, because they were considered U.S. government classified. They said do it. So I did it".[10]
Bruce Schneier observed that "It took the academic community two decades to figure out that the NSA 'tweaks' actually improved the security of DES."[11]

Despite the criticisms, DES was approved as a federal standard in November 1976, and published on 15 January 1977 as
FIPS
PUB 46, authorized for use on all unclassified data. It was subsequently reaffirmed as the standard in 1983, 1988 (revised as FIPS-46-1), 1993 (FIPS-46-2), and again in 1999 (FIPS-46-3), the latter prescribing "Triple DES" (see below). On 26 May 2002, DES was finally superseded by the Advanced Encryption Standard (AES), following
a public competition. On 19 May 2005, FIPS 46-3 was officially withdrawn, but
NIST
has approved Triple DES
through the year 2030 for sensitive government information.[12]

The algorithm is also specified in
ANSI
X3.92 (Now, X3 is now known as INCITS
and ANSI X3.92 as ANSI INCITS
92),[13]
NIST SP 800-67[12]
and ISO/IEC 18033-3[14]
(as a component of TDEA).

Another theoretical attack, linear cryptanalysis, was published in 1994, but it was a
brute force attack
in 1998 that demonstrated that DES could be attacked very practically, and highlighted the need for a replacement algorithm. These and other methods of cryptanalysis
are discussed in more detail later in this article.

The introduction of DES is considered to have been a catalyst for the academic study of cryptography, particularly of methods to crack block ciphers. According to a NIST retrospective about DES,

The DES can be said to have "jump started" the nonmilitary study and development of encryption algorithms. In the 1970s there were very few cryptographers, except for those in military or intelligence organizations, and little academic study of cryptography. There are now many active academic cryptologists, mathematics departments with strong programs in cryptography, and commercial information security companies and consultants. A generation of cryptanalysts has cut its teeth analyzing (that is trying to "crack") the DES algorithm. In the words of cryptographer
Bruce Schneier,[15]
"DES did more to galvanize the field of cryptanalysis than anything else. Now there was an algorithm to study." An astonishing share of the open literature in cryptography in the 1970s and 1980s dealt with the DES, and the DES is the standard against which every symmetric key algorithm since has been compared.[16]

The
FPGA
based parallel machine COPACOBANA
of the Universities of Bochum and Kiel, Germany, breaks DES in 9 days at $10,000 hardware cost.[18]
Within a year software improvements reduced the average time to 6.4 days.

Nov.

2008

The successor of
COPACOBANA, the RIVYERA machine reduced the average time to less than one single day.

For brevity, the following description omits the exact transformations and permutations which specify the algorithm; for reference, the details can be found in
DES supplementary material.

DES is the archetypal
block cipher — an
algorithm
that takes a fixed-length string of plaintext
bits and transforms it through a series of complicated operations into another ciphertext
bitstring of the same length. In the case of DES, the block size
is 64 bits. DES also uses a key
to customize the transformation, so that decryption can supposedly only be performed by those who know the particular key used to encrypt. The key ostensibly consists of 64 bits; however, only 56 of these are actually used by the algorithm. Eight bits are used solely for checking parity, and are thereafter discarded. Hence the effective
key length
is 56 bits, and it is always quoted as such.

The key is nominally stored or transmitted as 8
bytes, each with odd parity. According to ANSI X3.92-1981 (Now, known as ANSI
INCITS
92-1981), section 3.5:

One bit in each 8-bit byte of the
KEY
may be utilized for error detection in key generation, distribution, and storage. Bits 8, 16,..., 64 are for use in ensuring that each byte is of odd parity.

Like other block ciphers, DES by itself is not a secure means of encryption but must instead be used in a
mode of operation. FIPS-81 specifies several modes for use with DES.[19]
Further comments on the usage of DES are contained in FIPS-74.[20]

Decryption uses the same structure as encryption but with the keys used in reverse order. (This has the advantage that the same hardware or software can be used in both directions.)

The algorithm's overall structure is shown in Figure 1: there are 16 identical stages of processing, termed
rounds. There is also an initial and final
permutation, termed
IP
and FP, which are
inverses
(IP "undoes" the action of FP, and vice versa). IP and FP have no cryptographic significance, but were included in order to facilitate loading blocks in and out of mid-1970s 8-bit based hardware.[21]

Before the main rounds, the block is divided into two 32-bit halves and processed alternately; this criss-crossing is known as the
Feistel scheme. The Feistel structure ensures that decryption and encryption are very similar processes — the only difference is that the subkeys are applied in the reverse order when decrypting. The rest of the algorithm is identical. This greatly simplifies implementation, particularly in hardware, as there is no need for separate encryption and decryption algorithms.

The ⊕ symbol denotes the
exclusive-OR
(XOR) operation. The F-function
scrambles half a block together with some of the key. The output from the F-function is then combined with the other half of the block, and the halves are swapped before the next round. After the final round, the halves are swapped; this is a feature of the Feistel structure which makes encryption and decryption similar processes.

Expansion — the 32-bit half-block is expanded to 48 bits using the
expansion permutation, denoted
E
in the diagram, by duplicating half of the bits. The output consists of eight 6-bit (8 * 6 = 48 bits) pieces, each containing a copy of 4 corresponding input bits, plus a copy of the immediately adjacent bit from each of the input pieces to either side.

Key mixing — the result is combined with a
subkey
using an XOR operation. 16 48-bit subkeys — one for each round — are derived from the main key using the key schedule
(described below).

Substitution — after mixing in the subkey, the block is divided into eight 6-bit pieces before processing by the
S-boxes, or
substitution boxes. Each of the eight S-boxes replaces its six input bits with four output bits according to a non-linear transformation, provided in the form of a
lookup table. The S-boxes provide the core of the security of DES — without them, the cipher would be linear, and trivially breakable.

Permutation — finally, the 32 outputs from the S-boxes are rearranged according to a fixed
permutation, the
P-box. This is designed so that, after permutation, each S-box's output bits are spread across 4 different S boxes in the next round.

The alternation of substitution from the S-boxes, and permutation of bits from the P-box and E-expansion provides so-called "confusion and diffusion" respectively, a concept identified by
Claude Shannon
in the 1940s as a necessary condition for a secure yet practical cipher.

Figure 3 illustrates the
key schedule
for encryption — the algorithm which generates the subkeys. Initially, 56 bits of the key are selected from the initial 64 by Permuted Choice 1
(PC-1) — the remaining eight bits are either discarded or used as
parity
check bits. The 56 bits are then divided into two 28-bit halves; each half is thereafter treated separately. In successive rounds, both halves are rotated left by one or two bits (specified for each round), and then 48 subkey bits are selected by Permuted Choice 2
(PC-2) — 24 bits from the left half, and 24 from the right. The rotations (denoted by "<<<" in the diagram) mean that a different set of bits is used in each subkey; each bit is used in approximately 14 out of the 16 subkeys.

The key schedule for decryption is similar — the subkeys are in reverse order compared to encryption. Apart from that change, the process is the same as for encryption. The same 28 bits are passed to all rotation boxes.

Although more information has been published on the cryptanalysis of DES than any other block cipher, the most practical attack to date is still a brute force approach. Various minor cryptanalytic properties are known, and three theoretical attacks are possible which, while having a theoretical complexity less than a brute force attack, require an unrealistic number of
known
or chosen plaintexts
to carry out, and are not a concern in practice.

For any cipher, the most basic method of attack is
brute force — trying every possible key in turn. The
length of the key
determines the number of possible keys, and hence the feasibility of this approach. For DES, questions were raised about the adequacy of its key size early on, even before it was adopted as a standard, and it was the small key size, rather than theoretical cryptanalysis, which dictated a need for a replacement algorithm. As a result of discussions involving external consultants including the NSA, the key size was reduced from 128 bits to 56 bits to fit on a single chip.[22]

The EFF's US$250,000
DES cracking machine
contained 1,856 custom chips and could brute force a DES key in a matter of days — the photo shows a DES Cracker circuit board fitted with several Deep Crack chips.

In academia, various proposals for a DES-cracking machine were advanced. In 1977, Diffie and Hellman proposed a machine costing an estimated US$20 million which could find a DES key in a single day. By 1993, Wiener had proposed a key-search machine costing US$1 million which would find a key within 7 hours. However, none of these early proposals were ever implemented—or, at least, no implementations were publicly acknowledged. The vulnerability of DES was practically demonstrated in the late 1990s. In 1997,
RSA Security
sponsored a series of contests, offering a $10,000 prize to the first team that broke a message encrypted with DES for the contest. That contest was won by the DESCHALL Project, led by Rocke Verser,
Matt Curtin, and Justin Dolske, using idle cycles of thousands of computers across the Internet. The feasibility of cracking DES quickly was demonstrated in 1998 when a custom DES-cracker was built by the
Electronic Frontier Foundation
(EFF), a cyberspace civil rights group, at the cost of approximately US$250,000 (see EFF DES cracker). Their motivation was to show that DES was breakable in practice as well as in theory: "There are many people who will not believe a truth until they can see it with their own eyes. Showing them a physical machine that can crack DES in a few days is the only way to convince some people that they really cannot trust their security to DES." The machine brute-forced a key in a little more than 2 days search.

The next confirmed DES cracker was the COPACOBANA machine built in 2006 by teams of the
Universities of Bochum
and Kiel, both in
Germany. Unlike the EFF machine, COPACOBANA consists of commercially available, reconfigurable integrated circuits. 120 of these
field-programmable gate arrays
(FPGAs) of type XILINX Spartan-3 1000 run in parallel. They are grouped in 20 DIMM modules, each containing 6 FPGAs. The use of reconfigurable hardware makes the machine applicable to other code breaking tasks as well.[23]
One of the more interesting aspects of COPACOBANA is its cost factor. One machine can be built for approximately $10,000.[24]
The cost decrease by roughly a factor of 25 over the EFF machine is an example of the continuous improvement of digital hardware—see
Moore's law. Adjusting for inflation over 8 years yields an even higher improvement of about 30x. Since 2007,
SciEngines GmbH, a spin-off company of the two project partners of COPACOBANA has enhanced and developed successors of COPACOBANA. In 2008 their COPACOBANA RIVYERA reduced the time to break DES to less than one day, using 128 Spartan-3 5000's. Currently SciEngines RIVYERA holds the record in brute-force breaking DES, having utilized 128 Spartan-3 5000 FPGAs.[25]
Their 256 Spartan-6 LX150 model has further lowered this time.

There are three attacks known that can break the full 16 rounds of DES with less complexity than a brute-force search:
differential cryptanalysis
(DC), linear cryptanalysis (LC), and Davies' attack. However, the attacks are theoretical and are unfeasible to mount in practice[citation needed]; these types of attack are sometimes termed certificational weaknesses.

Linear cryptanalysis
was discovered by Mitsuru Matsui, and needs 243known plaintexts
(Matsui, 1993); the method was implemented (Matsui, 1994), and was the first experimental cryptanalysis of DES to be reported. There is no evidence that DES was tailored to be resistant to this type of attack. A generalization of LC — multiple linear cryptanalysis — was suggested in 1994 (Kaliski and Robshaw), and was further refined by Biryukov and others. (2004); their analysis suggests that multiple linear approximations could be used to reduce the data requirements of the attack by at least a factor of 4 (that is, 241
instead of 243). A similar reduction in data complexity can be obtained in a chosen-plaintext variant of linear cryptanalysis (Knudsen and Mathiassen, 2000). Junod (2001) performed several experiments to determine the actual time complexity of linear cryptanalysis, and reported that it was somewhat faster than predicted, requiring time equivalent to 239–241
DES evaluations.

Improved Davies' attack: while linear and differential cryptanalysis are general techniques and can be applied to a number of schemes, Davies' attack is a specialized technique for DES, first suggested by
Donald Davies
in the eighties, and improved by Biham and Biryukov
(1997). The most powerful form of the attack requires 250known plaintexts, has a computational complexity of 250, and has a 51% success rate.

There have also been attacks proposed against reduced-round versions of the cipher, that is, versions of DES with fewer than 16 rounds. Such analysis gives an insight into how many rounds are needed for safety, and how much of a "security margin" the full version retains.
Differential-linear cryptanalysis
was proposed by Langford and Hellman in 1994, and combines differential and linear cryptanalysis into a single attack. An enhanced version of the attack can break 9-round DES with 215.8
chosen plaintexts and has a 229.2
time complexity (Biham and others, 2002).

where
is the bitwise complement
of
denotes encryption with key
and
denote plaintext and ciphertext blocks respectively. The complementation property means that the work for a brute force attack
could be reduced by a factor of 2 (or a single bit) under a chosen-plaintext
assumption. By definition, this property also applies also to TDES cipher.[citation needed]

DES also has four so-called
weak keys. Encryption (E) and decryption (D) under a weak key have the same effect (see
involution):

or equivalently,

There are also six pairs of
semi-weak keys. Encryption with one of the pair of semiweak keys,
, operates identically to decryption with the other,
:

or equivalently,

It is easy enough to avoid the weak and semiweak keys in an implementation, either by testing for them explicitly, or simply by choosing keys randomly; the odds of picking a weak or semiweak key by chance are negligible. The keys are not really any weaker than any other keys anyway, as they do not give an attack any advantage.

DES has also been proved not to be a
group, or more precisely, the set
(for all possible keys ) under
functional composition
is not a group, nor "close" to being a group.[27]
This was an open question for some time, and if it had been the case, it would have been possible to break DES, and multiple encryption modes such as Triple DES
would not increase the security.

It is known that the maximum cryptographic security of DES is limited to about 64 bits, even when independently choosing all round subkeys instead of deriving them from a key, which would otherwise permit a security of 768 bits.

Concerns about security and the relatively slow operation of DES in
software
motivated researchers to propose a variety of alternative block cipher
designs, which started to appear in the late 1980s and early 1990s: examples include RC5,
Blowfish,
IDEA,
NewDES,
SAFER,
CAST5
and FEAL. Most of these designs kept the 64-bit
block size
of DES, and could act as a "drop-in" replacement, although they typically used a 64-bit or 128-bit key. In the Soviet Union
the GOST 28147-89
algorithm was introduced, with a 64-bit block size and a 256-bit key, which was also used in Russia
later.

DES itself can be adapted and reused in a more secure scheme. Many former DES users now use
Triple DES
(TDES) which was described and analysed by one of DES's patentees (see FIPS
Pub 46-3); it involves applying DES three times with two (2TDES) or three (3TDES) different keys. TDES is regarded as adequately secure, although it is quite slow. A less computationally expensive alternative is DES-X, which increases the key size by XORing extra key material before and after DES.
GDES
was a DES variant proposed as a way to speed up encryption, but it was shown to be susceptible to differential cryptanalysis.

On January 2, 1997, NIST announced that they wished to choose a successor to DES.[28]
In 2001, after an international competition, NIST selected a new cipher, the Advanced Encryption Standard
(AES), as a replacement.[29]
The algorithm which was selected as the AES was submitted by its designers under the name Rijndael. Other finalists in the NIST
AES competition
included RC6,
Serpent,
MARS, and
Twofish.